US1737458A - Quaternary ammonium compound and process of making same - Google Patents

Quaternary ammonium compound and process of making same Download PDF

Info

Publication number
US1737458A
US1737458A US294046A US29404628A US1737458A US 1737458 A US1737458 A US 1737458A US 294046 A US294046 A US 294046A US 29404628 A US29404628 A US 29404628A US 1737458 A US1737458 A US 1737458A
Authority
US
United States
Prior art keywords
quaternary ammonium
acyl
aralkyl
aryl
acylated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US294046A
Inventor
Hartmann Max
Kagi Johann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Application granted granted Critical
Publication of US1737458A publication Critical patent/US1737458A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/30—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms containing a nitrogen-to-oxygen bond
    • C10M133/36—Hydroxylamines

Definitions

  • R means H, acyl or a hydrocarbon radical
  • R means acyl
  • R R and R mean a hydrocarbon radical such as alkyl, aryl, aralkyl
  • X means
  • the new products are easily soluble in water and in an alkaline or acid medium. They are applicable for technical and therapeutic purposes.
  • Ema/mple 1 380 parts of oleyl-diethylethylenediamine are mixed with 142 parts of methyl-iodide. Interaction sets in with much evolution of heat. The product forms an oleaginous mass.
  • An aqueous solution of the same product may be obtained directly by executing the reaction in presence of water. It may be employed for technical or therapeutic purposes, for example as liquid soap of great creaming properties being indifferent towards alkalies or acids.
  • Example 3 Z 382 parts ofstearyl-diethylethylenediamine are melted and stirred strongly with 126- parts of dimethylsulfate. The product of the reaction forms a mass resembling soap.
  • Example 4 380 parts of oleyl-diethylethylenediamine are mixed with 142 parts of benzylchloride and heated at about 100- C. After about 7 hours the benzylchloride has disappeared. The new oleaginous product dissolves easily in water.
  • Emample 5 (wherein R means H, acyl or a hydrocarbon radical, R means acyl, R and R mean the hydrocarbon radicals alkyl, aryl or aralkyl and n a whole number) with any alkylating agent.
  • R means oleyl
  • R and R mean the hydrocarbon radicals alkyl, aryl or aralkyl

Description

Patented Nov. 26, 1929 UNITED STATES PATENT OFFICE MAX. HABTMANN AND JOHANN KKGI, OF BAS EL, SWITZERLAND, ASBIGNOBB TO 80- CIE'IY OF CHEMICAL INDUSTRY IN BASLE, OI BASEL, SWITZERLAND QUATERNARY AMMONIUM COMPOUND AND PROCESS OF MAKING SAME No Drawing. Application filed July 19, 1928, Serial No. 294,046, and in Switzerland July 26, 1927.
The invention relates to the manufacture of new quaternary ammonium compounds of acylated alkylenediamines of the general formula (wherein R means H, acyl or a hydrocarbon radical, R means acyl, R R and R mean a hydrocarbon radical such as alkyl, aryl, aralkyl, X means any monovalent anion and n a=-"wh0le number) and consists in treating mono-acylated or unsymmetrical diacylated alkylenediamines, such as are described in the U. S. specification No. 1,534,525, with an alkylating agent such as dimethyl-suIfate, methyliodide,benzylchloride,p-toluene-ethylsulfonate and so on.
These new products have pronounced soaping properties even in alkaline solution, whilst the compounds described in the U. S. specification 1,534,525 have thev disadvantage of being precipitated from their solutions by means of alkalies.
The new products are easily soluble in water and in an alkaline or acid medium. They are applicable for technical and therapeutic purposes.
The following examples illustrate the invention, the parts being by weight Ema/mple 1 380 parts of oleyl-diethylethylenediamine are mixed with 142 parts of methyl-iodide. Interaction sets in with much evolution of heat. The product forms an oleaginous mass.
I Emample $2 380 parts of oleyl-diethylethylenediamine are mixed with 126 parts of dimethylsulfate and the whole is strongly stirred for some time. After cooling the new product remains as a viscous oil, Very soluble in water and in alkaline or acid medium.
An aqueous solution of the same product may be obtained directly by executing the reaction in presence of water. It may be employed for technical or therapeutic purposes, for example as liquid soap of great creaming properties being indifferent towards alkalies or acids.
' Example 3 Z 382 parts ofstearyl-diethylethylenediamine are melted and stirred strongly with 126- parts of dimethylsulfate. The product of the reaction forms a mass resembling soap.
Example 4 380 parts of oleyl-diethylethylenediamine are mixed with 142 parts of benzylchloride and heated at about 100- C. After about 7 hours the benzylchloride has disappeared. The new oleaginous product dissolves easily in water.
Emample 5 (wherein R means H, acyl or a hydrocarbon radical, R means acyl, R and R mean the hydrocarbon radicals alkyl, aryl or aralkyl and n a whole number) with any alkylating agent.
2. The process of manufacturing new quaternary ammonium compounds by treating an acylated diamine of the general formula N.CH:.CH:.N R1 R8 (wherein R means H, acyl or a hydrocarbon radical, R means acyl, R and R mean the hydrocarbon radicals alkyl, aryl or aralkyl) with any alkylating agent.
3. The process of manufacturing new quaternary ammonium compounds by treating an acylated djamine of the general formula (wherein R means acyl, R andR mean the hydrocarbon radicals alkyl, aryl or aralkyl) with any alkylating agent.
4. The process of manufacturing new quaternary ammonium compounds by treating an acylated diamine of the general formula (wherein R means an aliphatic acyl, R and R mean the hydrocarbon radicals alkyl, aryl or aralkyl) with any alkylating agent.
5. The process of manufacturing new quaterinary ammonium compounds by treating an acylated diamine of the general formula H R: N.CH:.CH:.N
(wherein R means oleyl, R and R mean the hydrocarbon radicals alkyl, aryl or aralkyl) with any alkylating agent.
6. The process of manufacturing new quaternary ammonium compounds by treating an acylated diamine of the general formula (wherein R means oleyl) with any alkaylating agent.
7. The process of manufacturing monooleyl diethyl-methyl ethylenedia-mmonium methylsulfate by treating mono-oleyl-diethylethylenediamine of the formula with dimethylsulfate.
8. As new products the quaternary ammonium compounds of acylated alkylenediamines of the formula (wherein R means H, acyl or a hydrocarbon radical, R means acyl, R R and R mean the hydrocarbon radicals alkyl, aryl, aralkyl, X means any monovalent anion and n a whole number), which products are soluble in water and in alkaline or in acid medium and have pronounced soaping properties.
9. As new products the quaternary ammonium compounds of acylated alkylenediamines of the general formula (wherein R means H, acyl or hydrocarbon radical, R means acyl, R R and R mean the hydrocarbon radicals, alkyl, aryl, aralkyl and X means any monovalent anion), which products are soluble in water and in alkaline or in acid medium and have pronounced soaping properties.
10. As new products the quaternary ammonium compounds of acylated alyklenediamines of the general formula (wherein R means an aliphatic acyl, R R and R mean the hydrocarbon radicals alkyl, aryl, aralkyl and X means and monovalent anion), which products are soluble in water and in alkaline or in acid medium and have pronounced soaping properties.
12. As new products the quaternary am monium compounds of acylated alkylenediamines of the general formula H Ra NDHLCHaN RaJ X 34 R5 (wherein R means oleyl, R R and R mean the hydrocarbon radicals alkyl, aryl, aralkyl and X means any monovalent anion), which products are soluble in water and in alkaline or in acid medium and have pronounced soaping properties.
13. As new products the quaternary ammonium compounds of acylated alkylenediamines of the general formula (wherein R means oleyl, R the hydrocarbon radicals alkyl, aryl, aralkyl and X any monovalent anion), which products are soluble in water and in alkaline or in acid medium and have pronounced soaping properties.
14. As new products the mono-oleyl-diethyl -methylethylene diammonium methylsulfate of the formula which constitutes a yellowish viscous oil, very soluble in water and in alkaline or in acid medium and has pronounced soaping properties. 1
In witness whereof we have hereunto signed our names this 7th day of July, 1928.
MAX HARTMANN.
J OHANN KAGI.
US294046A 1927-07-26 1928-07-19 Quaternary ammonium compound and process of making same Expired - Lifetime US1737458A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1737458X 1927-07-26

Publications (1)

Publication Number Publication Date
US1737458A true US1737458A (en) 1929-11-26

Family

ID=4566087

Family Applications (1)

Application Number Title Priority Date Filing Date
US294046A Expired - Lifetime US1737458A (en) 1927-07-26 1928-07-19 Quaternary ammonium compound and process of making same

Country Status (1)

Country Link
US (1) US1737458A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2432127A (en) * 1943-10-16 1947-12-09 Rayonier Inc Method of improving the processing of refined chemical pulp into viscose
US2459062A (en) * 1944-02-08 1949-01-11 American Cyanamid Co Quaternary ammonium compounds
US2496640A (en) * 1944-05-18 1950-02-07 Nopco Chem Co Fat liquoring and alum tanning
US2496641A (en) * 1946-11-12 1950-02-07 Nopco Chem Co Fat liquoring and alum tanning
US2589674A (en) * 1947-05-24 1952-03-18 American Cyanamid Co Aliphatic amido propyl quaternary ammonium salts
US2644003A (en) * 1950-02-24 1953-06-30 Geigy Ag J R Quaternary ammonium compounds and their manufacture
US2654758A (en) * 1948-08-30 1953-10-06 Schering Corp Substituted ethylenediamine derivatives
US2742464A (en) * 1951-04-25 1956-04-17 Koebner Adolf Production of capillary active amine-amides
US3869483A (en) * 1972-06-23 1975-03-04 Us Agriculture Quaternary ammonium salts of n-substituted palmitamides
US4342706A (en) * 1980-09-08 1982-08-03 Van Dyk & Company, Inc. Benzene sulfonate quaternary ammonium salts
WO1991015474A1 (en) * 1990-03-31 1991-10-17 The Procter & Gamble Company Peroxy acid bleach precursors and detergent compositions containing them

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2432127A (en) * 1943-10-16 1947-12-09 Rayonier Inc Method of improving the processing of refined chemical pulp into viscose
US2459062A (en) * 1944-02-08 1949-01-11 American Cyanamid Co Quaternary ammonium compounds
US2496640A (en) * 1944-05-18 1950-02-07 Nopco Chem Co Fat liquoring and alum tanning
US2496641A (en) * 1946-11-12 1950-02-07 Nopco Chem Co Fat liquoring and alum tanning
US2589674A (en) * 1947-05-24 1952-03-18 American Cyanamid Co Aliphatic amido propyl quaternary ammonium salts
US2654758A (en) * 1948-08-30 1953-10-06 Schering Corp Substituted ethylenediamine derivatives
US2644003A (en) * 1950-02-24 1953-06-30 Geigy Ag J R Quaternary ammonium compounds and their manufacture
US2742464A (en) * 1951-04-25 1956-04-17 Koebner Adolf Production of capillary active amine-amides
US3869483A (en) * 1972-06-23 1975-03-04 Us Agriculture Quaternary ammonium salts of n-substituted palmitamides
US4342706A (en) * 1980-09-08 1982-08-03 Van Dyk & Company, Inc. Benzene sulfonate quaternary ammonium salts
WO1991015474A1 (en) * 1990-03-31 1991-10-17 The Procter & Gamble Company Peroxy acid bleach precursors and detergent compositions containing them

Similar Documents

Publication Publication Date Title
US1737458A (en) Quaternary ammonium compound and process of making same
US2635112A (en) Process for producing aminomethylphosphonic acid compounds
US2113606A (en) Quaternary ammonium compounds
US2268395A (en) Quaternary ammonium compounds
US3177218A (en) Methylene-bis(2-guanidino-4-methylquinazoline)
JPS5810542A (en) Quaternary ammonium salt and manufacture
US2258321A (en) Condensation products of amines and monoalkylol cyanamides
US1947951A (en) Acidyl polyalkylene polyamines
US1924698A (en) Alkylated acidyl polyalkylene polyamines
US1867022A (en) Wetting, cleansing, and emulsifying agents and process of making same
US2131210A (en) Accelerator for the vulcanization of rubber
US3093666A (en) Isothiouronium compounds
US2520275A (en) Aromatic diquaternary ammonium compounds
US2375659A (en) Alkoxypropylamine condensation products
US2127476A (en) Production of quaternary ammonium bases
US1726647A (en) Substituted dithiocarbamates and method of making same
US2014421A (en) Accelerator for the vulcanization of rubber
US1923179A (en) Treatment of textiles and agents therefor
US2609392A (en) Cinnamyl quaternary ammonium compounds
US2299756A (en) Quaternary ammonium derivative
US2251940A (en) Sulphonic derivatives
DE1240872B (en) Process for the production of water-soluble, capillary-active ampholytes that can be used as washing and cleaning agents and as foam stabilizers
US2325331A (en) Amino-acid amide derivatives and a process for their manufacture
US2104068A (en) Quaternary ammonium salts of mercapto-arylenethiazoles
US2524547A (en) Fungicidal mercury compounds and methods of making same